CN114717056B - Method for acid-catalyzed methyl esterification of grease - Google Patents
Method for acid-catalyzed methyl esterification of grease Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 91
- 238000005886 esterification reaction Methods 0.000 title claims abstract description 71
- 230000032050 esterification Effects 0.000 title claims abstract description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 68
- 239000004519 grease Substances 0.000 title claims abstract description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 129
- 239000002904 solvent Substances 0.000 claims abstract description 73
- 239000002131 composite material Substances 0.000 claims abstract description 69
- 239000000243 solution Substances 0.000 claims abstract description 46
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000006228 supernatant Substances 0.000 claims abstract description 35
- 239000012488 sample solution Substances 0.000 claims abstract description 28
- 239000011259 mixed solution Substances 0.000 claims abstract description 20
- 238000010335 hydrothermal treatment Methods 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000003377 acid catalyst Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 12
- 238000001816 cooling Methods 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 238000007865 diluting Methods 0.000 claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 57
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 35
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 35
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 28
- 239000003153 chemical reaction reagent Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 12
- 235000011152 sodium sulphate Nutrition 0.000 claims description 12
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- -1 methanol compound Chemical class 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 abstract description 5
- 238000010992 reflux Methods 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
- 238000007796 conventional method Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 43
- 235000019198 oils Nutrition 0.000 description 42
- 239000000194 fatty acid Substances 0.000 description 37
- 235000014113 dietary fatty acids Nutrition 0.000 description 35
- 229930195729 fatty acid Natural products 0.000 description 35
- 150000004665 fatty acids Chemical class 0.000 description 34
- 239000003925 fat Substances 0.000 description 32
- 235000019197 fats Nutrition 0.000 description 32
- WCYAALZQFZMMOM-UHFFFAOYSA-N methanol;sulfuric acid Chemical compound OC.OS(O)(=O)=O WCYAALZQFZMMOM-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000007789 gas Substances 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 18
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 17
- 235000012424 soybean oil Nutrition 0.000 description 16
- 239000003549 soybean oil Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 239000000523 sample Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 238000010406 interfacial reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000014107 unsaturated dietary fats Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention provides a method for acid-catalyzed methyl esterification of grease, which comprises the following steps: (1) Mixing the grease, the acidified methanol composite solution and the composite solvent uniformly to obtain a mixed solution; (2) Performing hydrothermal treatment on the mixed solution obtained in the step (1), and cooling and extracting after the hydrothermal treatment is finished to obtain supernatant and raffinate; (3) Removing water and diluting the supernatant obtained in the step (2) to obtain a sample solution; the compound solvent comprises benzene solvent and aliphatic hydrocarbon solvent. According to the method for acid-catalyzed methyl esterification of the grease, provided by the invention, the composite solvent is introduced, and the reasonable concentration of the acid catalyst is selected by optimizing the proportion of alcohol to the grease and the composite organic solvent, so that the methyl esterification efficiency of the grease is effectively improved, the conventional method for heating reflux methyl esterification can be replaced, and the application range is wide.
Description
Technical Field
The invention belongs to the technical field of physicochemical analysis and test, relates to a method for methyl esterification of grease, and in particular relates to a method for acid-catalyzed methyl esterification of grease.
Background
The main component of the dietary oil is triglyceride which is glyceride formed by esterifying three hydroxyl groups of glycerol with three fatty acid molecules. Wherein the type and content ratio of fatty acids determine the quality and nutritional value of the oil. The fatty acid in the oil is measured by a direct method and an indirect method, wherein the direct method mainly comprises a gas chromatography-mass spectrometry, a liquid chromatography-mass spectrometry, an infrared spectrometry, a nuclear magnetic resonance method and the like; the indirect method is to derive fatty acid in the fat component into fatty acid methyl ester form, and determine it by gas chromatography-hydrogen ion flame method (GC-FID).
CN 102749396a discloses a method for detecting fatty acid content by gas chromatography-mass spectrometry, which comprises the following specific steps: 1) Treatment of animal tissue samples, 2) extraction, saponification and methyl esterification of fatty acids; 3) Determining conditions for detecting fatty acids by GC-MS; 4) And (5) data analysis and sample identification. The method for detecting the fatty acid content in animal tissues has the characteristics of simple operation, low detection limit, good experimental reproducibility, visual and reliable experimental data and the like, and is particularly suitable for detecting trace samples. However, the application range of the gas chromatography-mass spectrometry is limited, and the measurement requirement of partial fatty acid cannot be met.
CN 101504362a discloses a method for rapidly detecting trans-fatty acid content in edible oil based on near infrared spectrum technology, which is realized by the following steps: 1. establishing a correction set sample spectrum; 2. preprocessing spectral data; 3. measuring basic data; 4. establishing a correction model; 5. verifying a correction model; 6. and (5) analyzing the sample to be tested. The method provided by the invention is used for detecting the trans-fatty acid content in the edible oil and fat, so that the detection period can be effectively shortened. But the detection accuracy of the infrared spectrometry is to be improved
Kou Xiuying and the like, by researching a fatty and fatty acid methyl esterification method, acid catalysis is obtained, and is applicable to esterification of free fatty acid and esterified fat; the alkali method is only suitable for esterifying fat and is not suitable for esterifying free fatty acid, and the methyl esterification effect of fatty acid of the 1% sulfuric acid-methanol esterification method can reach 72.81% (Kou Xiuying, research on the methyl esterification method of fat and fatty acid [ J ], food research and development 2005, 26 (2): 2), but the methyl esterification efficiency of the method is still lower.
Gas phase analysis of fatty acid methyl esters of animal and vegetable fats and oils according to ISO 12966-2:2016 part 2: the sulfuric acid catalysis method in the preparation of fatty acid methyl ester is as follows: the volume ratio of sulfuric acid to methanol is 1:15, the mass volume ratio of grease to acidified methanol is 100mg:400 mu L, the reaction vessel is a flame-burnt sealed glass ampoule bottle, and the raw materials react for 3 hours at the temperature of 100-110 ℃. The ISO method reaction vessel is complicated to manufacture and the reaction process is too long.
Aiming at the defects of the prior art, a high-efficiency, rapid and accurate method for acid-catalyzed methyl esterification of grease needs to be provided.
Disclosure of Invention
The invention aims to provide a method for acid-catalyzed methyl esterification of grease, which is characterized in that a composite organic solvent is introduced in the transesterification reaction of the grease and methanol to raise the interface reaction into a three-dimensional reaction in solution, so that the reaction speed and the methyl esterification efficiency are improved.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
the invention provides a method for acid-catalyzed methyl esterification of grease, which comprises the following steps:
(1) Mixing the grease, the acidified methanol composite solution and the composite solvent uniformly to obtain a mixed solution;
(2) Performing hydrothermal treatment on the mixed solution obtained in the step (1), and cooling and extracting after the hydrothermal treatment is finished to obtain supernatant and raffinate;
(3) Removing water and diluting the supernatant obtained in the step (2) to obtain a sample solution;
the compound solvent comprises benzene solvent and aliphatic hydrocarbon solvent.
According to the method for methyl esterification of the grease, the grease and the methanol undergo transesterification reaction under the action of the acid catalyst, and the interfacial reaction of the grease and the methanol is increased to be a three-dimensional reaction in the solution by introducing the composite organic solvent of the benzene solvent and the aliphatic hydrocarbon solvent, so that the reaction rate is accelerated; meanwhile, the selection of the composite solvent has great influence on the reaction rate and the conversion degree, and the invention provides proper component proportion and solvent type, thereby effectively improving the methyl esterification efficiency of the grease and shortening the reaction time.
Preferably, the mass-to-volume ratio of the oil and fat to the acidified methanol complex solution in step (1) is (45-55) mg/1 mL, for example 45 mg/1 mL, 48 mg/1 mL, 50 mg/1 mL, 52 mg/1 mL or 55 mg/1 mL, but not limited to the values listed, and other values not listed in the range of values are equally applicable.
The mass-volume ratio of the grease to the acidified methanol composite liquid can ensure that the reaction is fully carried out in the range, the ratio is too high, and the methyl esterification efficiency of the grease is reduced; too low a ratio affects consistency of batch operation, sample uniformity and precision.
Preferably, the volume ratio of the acidified methanol complex solution to the complex solvent in step (1) is 1 (0.5-1), for example, it may be 1:0.5, 1:0.6, 1:0.7, 1:0.8, 1:0.9 or 1:1, but not limited to the recited values, and other non-recited values within the range of values are equally applicable.
Preferably, the fat of step (1) comprises any one or a combination of at least two of an oil, a fat or a fat derivative, typically but not limited to a combination of an oil and a fat, a combination of a fat and a fat derivative, a combination of an oil and a fat derivative, or a combination of an oil, a fat and a fat derivative.
Preferably, the acidified methanol complex liquor of step (1) comprises a volume ratio (0.035-0.055) of acid catalyst to methanol of 1, for example, 0.035:1, 0.04:1, 0.045:1, 0.05:1 or 0.055:1, but not limited to the values recited, as well as other non-recited values within the range of values.
Because the dosage of the acid catalyst is small and the addition amount of the acid catalyst is not easy to control, the acid catalyst is diluted by the reaction component methanol to prepare the acidified methanol composite liquid, and the ratio of the acid catalyst to the methanol is in a preferred range, so that the catalytic effect of the catalyst can be effectively ensured.
Preferably, the acid catalyst comprises sulfuric acid, and the mass percentage of the sulfuric acid is 95-98%.
Preferably, the volume ratio of the benzene solvent to the aliphatic hydrocarbon solvent in the step (1) is (3-5): 1, which may be, for example, 3:1, 3.5:1, 4:1, 4.5:1 or 5:1, but is not limited to the recited values, and other non-recited values within the range of values are equally applicable.
Preferably, the benzene solvent comprises toluene.
Preferably, the aliphatic hydrocarbon solvent comprises isooctane and/or n-heptane, preferably isooctane.
According to the composite solvent provided by the invention, on one hand, the interfacial reaction of the grease and the methanol can be raised into a three-dimensional reaction in the solution by utilizing the characteristics of mutual solubility of the toluene and the methanol, mutual solubility of the isooctane and the grease and mutual solubility of the toluene and the isooctane, so that the reaction rate is accelerated; on the other hand, the toluene with a higher boiling point increases the temperature range of the reaction, so that the reaction efficiency is further accelerated, meanwhile, the unsaturated bonds in the fatty acid are protected by the weak reducibility of the toluene, and the tolerance degree of the toluene to the sulfuric acid concentration is improved.
Preferably, the hydrothermal temperature in step (2) is 75-85 ℃, for example, 75 ℃, 78 ℃, 80 ℃, 82 ℃ or 85 ℃, but not limited to the recited values, and other values not recited in the numerical range are equally applicable.
Preferably, the hydrothermal time of step (2) is 50-60min, for example, 50min, 53min, 55min, 58min or 60min, but not limited to the recited values, and other non-recited values in the range of values are equally applicable.
Preferably, during the hydrothermal process of step (2), vortex for 9-11s every 18-22 min.
In the hydrothermal process, vortex is performed every 18-22min, for example, 18min, 19min, 20min, 21min or 22min, but the method is not limited to the listed values, and other values not listed in the numerical range are applicable.
In the hydrothermal process, vortex is carried out for 9-11s, for example, 9s, 9.5s, 10s, 10.5s or 11s every 18-22min, but the method is not limited to the recited values, and other non-recited values in the numerical range are equally applicable.
Preferably, the reagent extracted in step (2) comprises an extractant to separation aid in a volume ratio of 1 (1-3), such as 1:1, 1:1.5, 1:2, 1:2.5 or 1:3, but not limited to the recited values, and other non-recited values within the range of values are equally applicable.
Preferably, the extractant comprises isooctane and/or n-heptane.
Preferably, the separation aid comprises a sodium chloride solution, preferably a saturated sodium chloride solution.
The invention adds proper saturated sodium chloride solution during extraction, and can reduce the solubility of organic matters and extraction solvent in aqueous solution by utilizing salting-out effect, thereby improving the extraction effect.
Preferably, the volume ratio of the extractant to the complex solvent is (1-3): 1, which may be, for example, 1:1, 1.5:1, 2:1, 2..5:1 or 3:1, but is not limited to the recited values, and other non-recited values within the range of values are equally applicable.
Preferably, the extraction time in step (2) is 14-16s, for example, 14s, 14.5s, 15s, 15.5s or 16s, but not limited to the recited values, and other non-recited values within the range of values are equally applicable.
Preferably, the removing water of step (3) comprises: and uniformly mixing the supernatant with a water removal reagent to obtain a water removal solution.
Preferably, the mass to volume ratio of the water removal reagent to the supernatant is (1-2) g/1 mL, for example, 1 g/1 mL, 1.25 g/1 mL, 1.5 g/1 mL, 1.75 g/1 mL or 2 g/1 mL, but not limited to the recited values, and other non-recited values within the range of values are equally applicable.
Preferably, the water removal agent comprises sodium sulfate.
Preferably, the supernatant obtained by re-extracting the raffinate obtained in the step (2) is combined with the supernatant obtained in the step (2).
When the absolute content of fatty acid is measured, the raffinate is extracted again, so that the accuracy of measurement of the medium-short chain fatty acid can be effectively improved.
Preferably, the dilution in step (3) comprises 2-10 times dilution with an organic solvent, which may be, for example, 2-fold, 3-fold, 4-fold, 5-fold, 6-fold, 7-fold, 8-fold, 9-fold or 10-fold, but is not limited to the recited values, and other non-recited values within the range of values are equally applicable, preferably 2-5-fold.
When the absolute content of fatty acid is measured, the organic solvent is used for diluting the water solution by 2-5 times.
Preferably, the organic solvent comprises isooctane.
As a preferred technical solution of the method according to the invention, the method comprises the steps of:
(1) Mixing the grease, the acidified methanol composite solution and the composite solvent uniformly to obtain a mixed solution;
the mass volume ratio of the grease to the acidified methanol composite liquid is (45-55) mg to 1mL; the volume ratio of the acidified methanol composite liquid to the composite solvent is 1 (0.5-1); the acidified methanol compound liquid comprises an acid catalyst and methanol with the volume ratio of (0.035-0.055) 1; the compound solvent comprises benzene solvent and aliphatic hydrocarbon solvent with volume ratio of (3-5): 1;
(2) Carrying out hydrothermal treatment at 75-85 ℃ for 50-60min on the mixed solution obtained in the step (1), and cooling and extracting for 14-16s after the hydrothermal treatment is finished to obtain supernatant and raffinate;
in the hydrothermal process, vortex is carried out for 9-11s every 18-22 min; the extracted reagent comprises an extracting agent and a separation auxiliary agent in a volume ratio of (1-3); the volume ratio of the extractant to the composite solvent is (1-3): 1;
(3) The supernatant obtained in the step (2) is dehydrated by a water removal reagent and diluted by an organic solvent to obtain a sample solution;
the mass volume ratio of the water removing agent to the supernatant is (1-2) g to 1mL.
Compared with the prior art, the invention has the following beneficial effects:
according to the method for acid-catalyzed methyl esterification of the grease, provided by the invention, the compound solvent of the benzene solvent and the aliphatic hydrocarbon solvent is introduced, so that the interfacial reaction of the grease and the methanol is converted into the three-dimensional reaction in the solution, the reaction rate is accelerated, and the reasonable concentration of the acid catalyst is selected by optimizing the ratio of the alcohol to the grease to the compound organic solvent, so that the methyl esterification efficiency of the grease can reach 95%. The method provided by the invention is economical and efficient, can replace the conventional heating reflux methyl esterification method, and has wide application range.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The sample solutions obtained by the acid-catalyzed fat methyl esterification methods provided in the following examples and comparative examples were measured by a gas chromatograph under the following chromatographic conditions: agilent J & W DB-FastFAME medium content cyanopropyl stationary phase capillary column (30 m×0.25mm,0.25 μm); the temperature of the sample inlet is 250 ℃; the split ratio is 50:1; the sample injection amount is 1 mu L; the initial temperature of the column temperature box is 80 ℃, and the temperature rise program is as follows: maintaining at 80deg.C for 0.5min; raising the temperature to 165 ℃ at 40 ℃/min, and keeping for 1min; then raising the temperature to 230 ℃ at 4 ℃/min, and keeping the temperature for 8min; the carrier gas is nitrogen; a constant flow mode with a flow rate of 0.4mL/min, a pressure of 6.0138 psi; the FID heater is 260 ℃, the hydrogen flow is 30mL/min, the air flow is 400mL/min, and the tail gas flow is 15mL/min.
Example 1
The embodiment provides a method for acid-catalyzed methyl esterification of grease, which comprises the following steps:
(1) Uniformly mixing GBW (E) 100120 soybean oil fatty acid component analysis standard substance, sulfuric acid-methanol composite solution and toluene-isooctane composite solvent to obtain mixed solution;
the mass volume ratio of the GBW (E) 100120 soybean oil fatty acid component analysis standard substance to the sulfuric acid-methanol composite solution is 50 mg/1 mL; the volume ratio of the sulfuric acid-methanol composite solution to the toluene-isooctane composite solvent is 1:0.5; the volume ratio of sulfuric acid to methanol in the sulfuric acid-methanol composite liquid is 0.045:1; the volume ratio of toluene to isooctane in the toluene-isooctane composite solvent is 4:1;
(2) Carrying out hydrothermal treatment at 80 ℃ for 55min on the mixed solution obtained in the step (1), and cooling and extracting for 15s after the hydrothermal treatment is finished to obtain supernatant and raffinate;
in the hydrothermal process, vortex for 10s every 20 min; the extracted reagent is isooctane and saturated sodium chloride solution with the volume ratio of 1:2; the volume ratio of the isooctane to the toluene-isooctane composite solvent is 2:1;
(3) The supernatant obtained in the step (2) is dehydrated by sodium sulfate and diluted by 4 times by isooctane to obtain a sample solution;
the mass-to-volume ratio of sodium sulfate to supernatant was 1.5 g/1 mL.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 95.4% and the methyl esterification efficiency of the oil was 95%.
Example 2
The embodiment provides a method for acid-catalyzed methyl esterification of grease, which comprises the following steps:
(1) Uniformly mixing GBW (E) 100120 soybean oil fatty acid component analysis standard substance, sulfuric acid-methanol composite solution and toluene-isooctane composite solvent to obtain mixed solution;
the mass volume ratio of the GBW (E) 100120 soybean oil fatty acid component analysis standard substance to the sulfuric acid-methanol composite solution is 48 mg/1 mL; the volume ratio of the sulfuric acid-methanol composite solution to the toluene-isooctane composite solvent is 1:0.8; the volume ratio of sulfuric acid to methanol in the sulfuric acid-methanol composite liquid is 0.04:1; the volume ratio of toluene to isooctane in the toluene-isooctane composite solvent is 3.5:1;
(2) Carrying out hydrothermal treatment at 78 ℃ for 58min on the mixed solution obtained in the step (1), and cooling and extracting for 15.5s after the hydrothermal treatment is finished to obtain supernatant and raffinate;
in the hydrothermal process, vortex for 10.5s every 21 min; the extracted reagent is isooctane and saturated sodium chloride solution with the volume ratio of 1:1.5; the volume ratio of the isooctane to the toluene-isooctane composite solvent is 1.5:1;
(3) The supernatant obtained in the step (2) is dehydrated by sodium sulfate and diluted 5 times by isooctane to obtain a sample solution;
the mass to volume ratio of sodium sulfate to supernatant was 1.75 g/1 mL.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 92.3% and the methyl esterification efficiency of the oil was 92%.
Example 3
The embodiment provides a method for acid-catalyzed methyl esterification of grease, which comprises the following steps:
(1) Uniformly mixing GBW (E) 100120 soybean oil fatty acid component analysis standard substance, sulfuric acid-methanol composite solution and toluene-isooctane composite solvent to obtain mixed solution;
the mass volume ratio of the GBW (E) 100120 soybean oil fatty acid component analysis standard substance to the sulfuric acid-methanol composite solution is 52 mg/1 mL; the volume ratio of the sulfuric acid-methanol composite solution to the toluene-isooctane composite solvent is 1:0.6; the volume ratio of sulfuric acid to methanol in the sulfuric acid-methanol composite liquid is 0.05:1; the volume ratio of toluene to isooctane in the toluene-isooctane composite solvent is 4.5:1;
(2) Heating the mixed solution obtained in the step (1) at 82 ℃ for 53min, and cooling and extracting for 14.5s after the hydrothermal treatment is finished to obtain supernatant and raffinate;
in the hydrothermal process, vortex for 9.5s every 19 min; the extracted reagent is isooctane and saturated sodium chloride solution with the volume ratio of 1:2.5; the volume ratio of the isooctane to the toluene-isooctane composite solvent is 2.5:1;
(3) The supernatant obtained in the step (2) is dehydrated by sodium sulfate and diluted by 2 times by isooctane to obtain a sample solution;
the mass to volume ratio of sodium sulfate to supernatant was 1.25 g/1 mL.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 93.6% and the methyl esterification efficiency of the oil was 94%.
Example 4
The embodiment provides a method for acid-catalyzed methyl esterification of grease, which comprises the following steps:
(1) Uniformly mixing GBW (E) 100120 soybean oil fatty acid component analysis standard substance, sulfuric acid-methanol composite solution and toluene-isooctane composite solvent to obtain mixed solution;
the mass volume ratio of the GBW (E) 100120 soybean oil fatty acid component analysis standard substance to the sulfuric acid-methanol composite solution is 55 mg/1 mL; the volume ratio of the sulfuric acid-methanol composite solution to the toluene-isooctane composite solvent is 1:1; the volume ratio of sulfuric acid to methanol in the sulfuric acid-methanol composite liquid is 0.035:1; the volume ratio of toluene to isooctane in the toluene-isooctane composite solvent is 3:1;
(2) Carrying out hydrothermal treatment at 75 ℃ for 60min on the mixed solution obtained in the step (1), and cooling and extracting for 16s after the hydrothermal treatment is finished to obtain supernatant and raffinate;
in the hydrothermal process, vortex for 11s every 22 min; the extracted reagent is isooctane and saturated sodium chloride solution with the volume ratio of 1:1; the volume ratio of the isooctane to the toluene-isooctane composite solvent is 1:1;
(3) The supernatant obtained in the step (2) is dehydrated by sodium sulfate and diluted by 8 times by isooctane to obtain a sample solution;
the mass-to-volume ratio of sodium sulfate to supernatant was 2 g/1 mL.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 89.4% and the methyl esterification efficiency of the oil was 89%.
Example 5
The embodiment provides a method for acid-catalyzed methyl esterification of grease, which comprises the following steps:
(1) Uniformly mixing GBW (E) 100120 soybean oil fatty acid component analysis standard substance, sulfuric acid-methanol composite solution and toluene-isooctane composite solvent to obtain mixed solution;
the mass volume ratio of the GBW (E) 100120 soybean oil fatty acid component analysis standard substance to the sulfuric acid-methanol composite solution is 45 mg/1 mL; the volume ratio of the sulfuric acid-methanol composite solution to the toluene-isooctane composite solvent is 1:0.5; the volume ratio of sulfuric acid to methanol in the sulfuric acid-methanol composite liquid is 0.055:1; the volume ratio of toluene to isooctane in the toluene-isooctane composite solvent is 5:1;
(2) Carrying out hydrothermal treatment at 85 ℃ for 50min on the mixed solution obtained in the step (1), and cooling and extracting for 14s after the hydrothermal treatment is finished to obtain supernatant and raffinate;
in the hydrothermal process, vortex for 9s every 18 min; the extracted reagent is isooctane and saturated sodium chloride solution with the volume ratio of 1:3; the volume ratio of the isooctane to the toluene-isooctane composite solvent is 3:1;
(3) The supernatant obtained in the step (2) is dehydrated by sodium sulfate and diluted by 10 times by isooctane to obtain a sample solution;
the mass-volume ratio of sodium sulfate to supernatant was 1 g/1 mL.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 93.7% and the methyl esterification efficiency of the oil was 94%.
Example 6
The present example provides a method for acid-catalyzed methyl esterification of fats, which is different from example 1 in that the method is the same as example 1 except that the mass-volume ratio of the standard substance for analysis of soybean oil fatty acid component of GBW (E) 100120 to the sulfuric acid-methanol complex is 40 mg/1 mL.
The sample solution obtained in the embodiment has no obvious change in the methyl esterification efficiency of the grease as measured by a gas chromatograph, but too small a proportion of the grease can affect the uniformity and the operation precision of the sample, so that the sampling amount of the grease is not too small.
Example 7
The present example provides a method for acid-catalyzed methyl esterification of oil, which is different from example 1 in that the method is the same as example 1 except that the mass-volume ratio of the GBW (E) 100120 soybean oil fatty acid composition analysis standard substance to the sulfuric acid-methanol composite solution is 65 mg/1 mL.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 84.9% and the methyl esterification efficiency of the oil was 85%. In the method of the embodiment, the ratio of the grease is too large, and the methyl esterification efficiency of the grease is reduced.
Example 8
This example provides a method for acid-catalyzed methyl esterification of fats and oils, which differs from example 1 in that the method is the same as example 1 except that the volume ratio of sulfuric acid to methanol in the sulfuric acid-methanol composite solution is 0.03:1.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 68.2% and the methyl esterification efficiency of the oil was 68%. In the method described in this example, the catalyst ratio is too small, the reaction rate is reduced, and the methyl esterification efficiency of the oil is reduced.
Example 9
This example provides a method for acid-catalyzed methyl esterification of fats and oils, which differs from example 1 in that the method is the same as example 1 except that the volume ratio of sulfuric acid to methanol in the sulfuric acid-methanol composite solution is 0.06:1.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 65.4% and the methyl esterification efficiency of the oil was 65%. In the method, in the derivatization reaction process, the turbidity phenomenon of the solution after cooling exists, which indicates that the methyl esterification reaction is incomplete, and the methyl esterification efficiency of the grease is lower in the same time.
Example 10
This example provides a method for acid-catalyzed methyl esterification of fats and oils, which differs from example 1 in that the method is the same as example 1 except that the volume ratio of toluene to isooctane in the toluene-isooctane complex solvent is 2:1.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 65.1% and the methyl esterification efficiency of the oil was 65%. In the method described in this example, the toluene ratio is too small, and the reaction substrates methanol and isooctane are separated from each other to some extent, so that the methyl esterification efficiency of the oil is reduced.
Example 11
This example provides a method for acid-catalyzed methyl esterification of fats and oils, which differs from example 1 in that the method is the same as example 1 except that the volume ratio of toluene to isooctane in the toluene-isooctane complex solvent is 6:1.
The sample solution obtained in the embodiment has no obvious change in the methyl esterification efficiency of the grease as measured by a gas chromatograph, but toluene is slightly toxic, the steam density is high, and the sample solution is not easy to discharge after overflowing, so that the proportion of toluene is not excessively high.
Example 12
The present example provides a method for acid-catalyzed methyl esterification of fats and oils, which is different from example 1 in that the GBW (E) 100120 soybean oil fatty acid component analysis standard substance is replaced by microcapsule type fat powder fat and oils using palmitic acid as main fatty acid, and the rest is the same as example 1.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 91.2% and the methyl esterification efficiency of the oil was 91%.
Example 13
The present example provides a method for acid-catalyzed methyl esterification of fats and oils, which is different from example 1 in that the GBW (E) 100120 soybean oil fatty acid component analysis standard substance is replaced by micro-encapsulated fat powder fat and oil using lauric acid as main fatty acid, and the rest is the same as example 1.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 92.4% and the methyl esterification efficiency of the oil was 92%.
Example 14
The present example provides a method for acid-catalyzed methyl esterification of fats and oils, which is different from example 1 in that the GBW (E) 100120 soybean oil fatty acid component analysis standard substance is replaced with micro-encapsulated fat powder fat and oil mainly comprising medium-chain fatty acids c8:0 and c10:0, and essential fatty acid alpha-linolenic acid is disposed, and the rest is the same as example 1.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 92.3% and the methyl esterification efficiency of the oil was 92%.
Example 15
The present example provides a method for acid-catalyzed methyl esterification of oil, which is different from example 1 in that the GBW (E) 100120 soybean oil fatty acid component analysis standard substance is replaced by microcapsule type fat powder oil using alpha-linolenic acid as main fatty acid, and the rest is the same as example 1.
The sample solution obtained in this example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 95.4% and the methyl esterification efficiency of the oil was 95%.
Comparative example 1
This comparative example provides a method for acid-catalyzed methyl esterification of fats & oils, differing from example 1 in that the toluene-isooctane complex solvent is replaced with an isooctane solvent, and the rest is the same as example 1.
The sample solution obtained in this comparative example was measured by a gas chromatograph, and the total content of fatty acid methyl esters was 60.4% and the methyl esterification efficiency of the oil was 60%. Toluene is not added in the method, and as the grease dissolved in isooctane and the acidified methanol are in two phases and have poor intersolubility, heterogeneous catalysis reaction reduces the contact probability between methanol and grease molecule reaction substrates, so that the grease methyl esterification efficiency is reduced.
Comparative example 2
The comparison example provides a method for acid-catalyzed methyl esterification of oil in a water bath temperature field, which is different from the method in example 1 in that fatty acid determination is carried out according to an alkali-acid sequential methyl esterification method in GB5009.168-2016, the method adopts a methyl esterification method in a heating reflux temperature field, is not suitable for batch operation due to device limitation, and has complex steps and lower detection efficiency compared with a pure acid method.
In summary, according to the method for acid-catalyzed methyl esterification of oil provided by the invention, the toluene-isooctane compound solvent is introduced, so that the interfacial reaction of oil and methanol is converted into a three-dimensional reaction in solution, the reaction rate is accelerated, and the reasonable acid catalyst concentration is selected by optimizing the ratio of alcohol to oil and the compound organic solvent, so that the methyl esterification efficiency of oil can reach 95%. The method provided by the invention is economical and efficient, can replace the conventional heating reflux methyl esterification method, and has wide application range.
The applicant declares that the above is only a specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and it should be apparent to those skilled in the art that any changes or substitutions that are easily conceivable within the technical scope of the present invention disclosed by the present invention fall within the scope of the present invention and the disclosure.
Claims (21)
1. A method for acid-catalyzed methyl esterification of grease, which is characterized by comprising the following steps:
(1) Mixing the grease, the acidified methanol composite solution and the composite solvent uniformly to obtain a mixed solution;
(2) Performing hydrothermal treatment on the mixed solution obtained in the step (1), and cooling and extracting after the hydrothermal treatment is finished to obtain supernatant and raffinate;
(3) Removing water and diluting the supernatant obtained in the step (2) to obtain a sample solution;
the compound solvent in the step (1) comprises benzene solvent and aliphatic hydrocarbon solvent;
the volume ratio of the benzene solvent to the aliphatic hydrocarbon solvent is (3-5) 1;
the benzene solvent comprises toluene;
the aliphatic hydrocarbon solvent includes isooctane;
the acidified methanol compound liquid in the step (1) comprises an acid catalyst and methanol with the volume ratio of (0.035-0.055) 1;
the acid catalyst comprises sulfuric acid.
2. The method of claim 1, wherein the mass to volume ratio of the fat to acidified methanol complex liquor of step (1) is (45-55) mg to 1mL.
3. The method of claim 1, wherein the volume ratio of acidified methanol complex solution to complex solvent of step (1) is 1 (0.5-1).
4. The method of claim 1, wherein the grease of step (1) comprises any one or a combination of at least two of an oil, a fat, or a grease derivative.
5. The method of claim 1, wherein the hydrothermal temperature of step (2) is 75-85 ℃.
6. The method of claim 5, wherein the hydrothermal time of step (2) is 50-60 minutes.
7. The method of claim 6, wherein the hydrothermal process of step (2) is performed for 9-11 seconds every 18-22 minutes.
8. The method of claim 1, wherein the reagent extracted in step (2) comprises an extractant to separation aid in a volume ratio of 1 (1-3).
9. The method of claim 8, wherein the extractant comprises isooctane and/or n-heptane.
10. The method of claim 8, wherein the separation aid comprises a sodium chloride solution.
11. The method of claim 10, wherein the separation aid is a saturated sodium chloride solution.
12. The method of claim 8, wherein the volume ratio of extractant to complex solvent is (1-3): 1.
13. The method according to claim 1, wherein the extraction time of step (2) is 14-16s.
14. The method of claim 1, wherein the removing water of step (3) comprises: and uniformly mixing the supernatant with a water removal reagent to obtain a water removal solution.
15. The method of claim 14, wherein the mass to volume ratio of the water removal reagent to the supernatant is (1-2) g to 1mL.
16. The method of claim 14, wherein the water removal agent comprises sodium sulfate.
17. The process of claim 1, wherein the supernatant from the re-extraction of the raffinate from step (2) is combined with the supernatant from step (2).
18. The method of claim 1, wherein the diluting of step (3) comprises: diluting with organic solvent by 2-10 times.
19. The method of claim 18, wherein the diluting of step (3) comprises: diluting with organic solvent by 2-5 times.
20. The method of claim 19, wherein the organic solvent comprises isooctane.
21. The method according to claim 1, characterized in that it comprises the steps of:
(1) Mixing the grease, the acidified methanol composite solution and the composite solvent uniformly to obtain a mixed solution;
the mass volume ratio of the grease to the acidified methanol composite liquid is (45-55) mg to 1mL; the volume ratio of the acidified methanol composite liquid to the composite solvent is 1 (0.5-1); the acidified methanol compound liquid comprises an acid catalyst and methanol with the volume ratio of (0.035-0.055) 1; the acid catalyst comprises sulfuric acid; the compound solvent comprises benzene solvent and aliphatic hydrocarbon solvent with volume ratio of (3-5): 1; the benzene solvent comprises toluene; the aliphatic hydrocarbon solvent includes isooctane;
(2) Carrying out hydrothermal treatment at 75-85 ℃ for 50-60min on the mixed solution obtained in the step (1), and cooling and extracting for 14-16s after the hydrothermal treatment is finished to obtain supernatant and raffinate;
in the hydrothermal process, vortex is carried out for 9-11s every 18-22 min; the extracted reagent comprises an extracting agent and a separation auxiliary agent in a volume ratio of (1-3); the volume ratio of the extractant to the composite solvent is (1-3): 1;
(3) The supernatant obtained in the step (2) is dehydrated by a water removal reagent and diluted by an organic solvent to obtain a sample solution;
the mass volume ratio of the water removing agent to the supernatant is (1-2) g to 1mL.
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| CN104804878A (en) * | 2014-01-26 | 2015-07-29 | 李卫教 | Novel fatty acid methyl ester biodiesel production technology |
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| US10435633B2 (en) * | 2017-06-29 | 2019-10-08 | DPD Chemicals Inc. | Chemical rejuvenation process to permanently increase the API gravity of crude oil and bitumen |
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| GB1282926A (en) * | 1968-10-10 | 1972-07-26 | El Paso Products Co | Esterification and extraction process |
| CN1370140A (en) * | 1999-08-18 | 2002-09-18 | 戴维·加维·布鲁克·布考克 | Single-phase process for prodn. of fatty acid methyl esters from mixtures of triglycerides and fatty acids |
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